Polyglycol ethers of 7-ethyl-2-methyl-undecanol-4



Patented Nov. 11, 1952 2,617,830 POLYGLYCOL ETHERS oi? 7 ErHYL-2METHlKLfUNDECANOL- l Milton Kosniin, Dayton, ome, assienor-to mom santoChemical Companmstaliouis, Mot,- a/P001 poration of Delaware 'No'Drawing. Application luheiill, 1950,. I

Serial No. 171,560

5 Claims. (01. etcere)- The present invention relates to compoundshaving high surface-activity in aqueous solutions and to processes forpreparing the said compounds. V

In my prior Patents Nos 2,508,035 and 2,508,036. issued May 16, 1950, Ihave disclosed polyglycol ethers of certainbranched chain alcohols,namely, -ethyl 'no'nanol-2 and 2-n-propyl heptanol.

These products are produced by condensing of the present and relatedproducts the dtergency of Gardinol which is a commercial detergentproduct, by sulfating the mantis derived by hydrogenation of cocoanutoil fatty acids. 7

The detergency of thepresent andrelatedproducts-as determinedby the;Harris method isillus trated inthe following. table:

The present products are prepared by conethylene oxide with therespective alcohols. While densi-ng. ethyleneoxide:with-7-ethyle2-methylun- Detergency-Percent of Gardinol Prod'dt'lested 3" 5'0 300 5 3'06 v p. p.--m; p.-;p;;m.- p. ;p.-m;. -1). ppm.

n-"Dt'rad'canol-l-IO rnoles ethylene oxide; 110 109 ;1 27n-Tetradecanol+l5 .moles ethylene oxide- 102 103 108 1282-n-Ii5opyl-heptanol+5 moles ethylene- 50 45' '1-11 106 ox e:2-n-liopyl-heptanol+l0 moles ethylene 100' 78 99" 100 ox e. I I 2-n-15opyl-heptano1+l5 moles ethylene 102 87 93 100 0x1 e. s-Etlhlyllnonanol-2+5 moles ethylene 36 37 106 112 Oil 0. S-Etlayl nonanol-2+l0moles ethylene 114 110 111 oi: e. v i fi-Etihiyl unusual-21:15 molesethylene 110 101 101 116 ox e. 7-Ethyl 2-methyl undecanol-4+5 moles U120 I 7 120 128 ethylene oxide. 7-Ethy1e2-methyllundecanoI-4+10 moles124 v 127 131 :1-37 {ethylene oxide. ,4 i, v 7 Ethyl z-methyl undecanol4+15 moles .124 118 124 r187 ethylene oxide.

. z'lliabuilder consisted of40 parts of tetrasodium pyrophosphate, 40parts of starch forea'ch 20 parts of the active constituent.

these compounds show especially low andi therefore advantageous wetting.out speeds when aqueous solutions thereof are tested by the Bravestest, these products have been found to be somewhat deficient indetergency. v

I have now found that if at least 5, but less than 21, moles of ethyleneoxide be condensed with 7-ethyl-2-methyl undecanol-4 that a series ofproducts is obtained which exhibit not only excellentwetting-outproperties but also excellent detergency. As amatter of fact,the detergency of the present products is superior to that of thecorresponding products made from n-tetradecanol.

Relative detergency may be measured by any quantitative method; howeverfor the purpose of evaluating the present and related products I haveused the method described by Jay C. Harris in Soap and SanitaryChemicals for August and September 1943. By the application of thismethod it is possible to evaluate the detergency of a product in termsof any standard detergent For convenience I have compared the detergencydecanol-4 until at least 5mdles, but not in excess of 20 moles, havebeen condensed with the alcohol. The condensation may be carried out bymixing ethylene oxide either as gas or liquid with the alcohol andheating to a temperature of from 110 to C. The condensation reaction isaided by the presence of a catalyst. For this purpose any alkalinematerials, such l-as an alkali metal hydroxide or alcoholate may be;used.

The catalyst may be employed in relatively small amounts, usually from0.5% to 1% being employed. The catalyst is added to the liquid ale coholat the beginning of the reaction.

The products so produced are secondary alcohol ethers and are believedto have the structure:

CHsCHzCHaCHgCHCHrCHzCHCHgCHCHa Ha i loh sHi 3 where n is an integerhaving a value of from 4 to 19.

The following examples will further illustrate this invention:

* EXAMPLE 1' 150.9 g. (0.705 mole) of 7-ethyl-2-methyl undecanol-4 wasplaced in a glass flask, 1.5 g. of powdered KOH added and the contents.then heated to 120 C. A stream of gaseous ethylene oxide was passedinto the alcohol by means-of a gas dispersing tube and the streamcontinued until 155.1 g. of ethylene oxide had combined. The mass becamehot due to the exothermic reaction heat and the temperature wascontrolled bycooling the flask by the application of cold water to theexterior. In this way the temperature was maintained at about 150duringthe progress of the reaction. 7 v v r .The product obtained correspondsto the pentaethylene glycol ether of 7-ethyl-2-methyl undecanol-4.

EXAMPLE 2 A portion of the product obtained above, weighing-153 g., wasfurthertreated with 77.5 g. of ethylene oxide using the same apparatusas described above. The product obtained corresponded to thedecaethylene glycol ether of '7- ethyl-Z-methyl undecanol-4.

EXAMPLE 3 A of the product obtained in Example 2,

weighing 139.5 g.. was-treated with 46.7 g. of ethylene oxide in themanner described above. The product corresponded to the pentadecylethylene glycol ether of 'I-ethyl-Z-methyl un- 'decanol-4.,

The speed of wetting, as measured by the Draves test of the productswhen dissolved in water to form a 0.5% solution gave the follow- What Iclaim' is: ,1. C ompounds having the formula:

(1H, on;oniongomonomomonemotion.

. v Ha where n has a value of at least 4 but not in excess 2. Compoundshaving the formula:

5. The process which comprises passing ethylene oxide into'7-ethyl-2-methyl undecanol-4 at a temperature between C. and C. untilat least 5 moles, but less than 21 moles, of said ethylene oxide havecombined with each mole of said 7-ethyl-2-methyl undecanol-4.

MILTON KOSMIN.

REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATENTS Number Name Date 1,696,874 Young Dec. 25, 19281,970,578 Schoeller et al Aug. 21, 1934 2,226,119 De Groote et al. Dec.24, 1940 2,316,842 Coleman Apr. 20, 1943 2,355,823 Schlegel Aug. 15,1944 2,491,533 Swern Dec. 20, 1949 2,527,970 S0kO1' Oct. 31,1950

1. COMPOUND HAVING THE FORMULA: